(+/-)-α-cyclohexylidenemethyl-2-methylenebicyclo<3.1.0>hexane-1-methanol

Base Information

• Chemical Name: (+/-)-α-cyclohexylidenemethyl-2-methylenebicyclo<3.1.0>hexane-1-methanol
• CAS No.: 98758-86-2
• Molecular Formula: C₁₅H₂₂O
• Molecular Weight: 218.339
• Mol file: 98758-86-2.mol

Synonyms:(+/-)-α-cyclohexylidenemethyl-2-methylenebicyclo<3.1.0>hexane-1-methanol

Chemical Property of (+/-)-α-cyclohexylidenemethyl-2-methylenebicyclo<3.1.0>hexane-1-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-α-cyclohexylidenemethyl-2-methylenebicyclo<3.1.0>hexane-1-methanol

There total 11 articles about (+/-)-α-cyclohexylidenemethyl-2-methylenebicyclo<3.1.0>hexane-1-methanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.2%

bromomethylenecyclohexane (1121-49-9) + (+/-)-1-formyl-2-methylenebicyclo<3.1.0>hexane (88908-86-5,93601-52-6) → 2-Cyclohexylidene-1-((1R,5R)-2-methylene-bicyclo[3.1.0]hex-1-yl)-ethanol (88908-88-7,88931-01-5,98758-86-2)

Guidance literature:

With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/0040-4039(84)80016-7

Reference yield:

1-dibromomethyl-1-cyclohexanol (52183-68-3) → 2-Cyclohexylidene-1-((1R,5R)-2-methylene-bicyclo[3.1.0]hex-1-yl)-ethanol (88908-88-7,88931-01-5,98758-86-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 83.5 percent / Zn/acetic acid / CH₂Cl₂

2: 79.2 percent / t-butyllithium / tetrahydrofuran / -78 °C

With tert.-butyl lithium; acetic acid; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(84)80016-7

Reference yield:

2-oxo-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester (61996-11-0) → (+/-)-α-cyclohexylidenemethyl-2-methylenebicyclo<3.1.0>hexane-1-methanol (98758-86-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 47 percent / BuLi / tetrahydrofuran

2: LiAlH₄

3: pyridinium chlorochromate / CH₂Cl₂

4: 1) n-butyllithium / 1) THF, -20 deg C, 2 h; 2) -78 deg C, 30 min

With lithium aluminium tetrahydride; n-butyllithium; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)88315-X

upstream raw materials:

bromomethylenecyclohexane

(+/-)-1-formyl-2-methylenebicyclo<3.1.0>hexane

2-methylenebycyclo<3.1.0>hexane-1-carboxaldehyde

cyclohexanecarbaldehyde

Downstream raw materials:

(+/-)-(Z)-3-(2-cyclohexylidene-ethylidene)-4-methylenecyclohexanol

cyclohexylidene-((Z)-2-methylene-cyclohexyliden)-ethane